allylcinnamyldimethylammonium bromide | 76119-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: allylcinnamyldimethylammonium bromide
• 英文别名: (E)-N-allyl-N,N-dimethyl-3-phenylprop-2-en-1-aminium bromide；dimethyl-[(E)-3-phenylprop-2-enyl]-prop-2-enylazanium;bromide
• CAS: 76119-03-4
• 化学式: Br*C₁₄H₂₀N
• 分子量: 282.224
• InChiKey: VWRPVJCQYRJFSJ-YGCVIUNWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  allylcinnamyldimethylammonium bromide 在 盐酸 、 sodium methylate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 3-苯基己-5-烯醛
  参考文献：
  名称：

  涉及叶立德中间体的碱催化重排。第4部分。4-二甲基氨基丁烯的[1,3]σ重排和3-二甲基氨基己-1,5-二烯的[3,3]σ重排。

  摘要：

  9-二甲基氨基-9-（1-苯基烯丙基）芴的[1,3]σ重排（11）→（12）是170°的立体选择过程（84:16）。其他芴衍生物的类似[1,3]重排（16）→（17）显示，通过给电子9-取代基的顺序为O – > NMe 2 > OMe ，反应速率得到了提高。对于六-1，5-二烯的[3，3]上交重排（25）→（26），观察到类似的取代基作用。4-苯基，4,4-二甲基和3-二甲基氨基取代基在加速重排（25）→（26）的速率方面特别有效。

  DOI：

  10.1039/p19800001462
• 作为产物：
  描述：

  phenylpro-2-en-1-amonium chloride 、 3-溴丙烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以61%的产率得到allylcinnamyldimethylammonium bromide
  参考文献：
  名称：

  Supramolecular Ga₄L₆^12– Cage Photosensitizes 1,3-Rearrangement of Encapsulated Guest via Photoinduced Electron Transfer

  摘要：

  The K12Ga4L6 supramolecular cage is photoactive and enables an unprecedented photoreaction not observed in bulk solution. Ga4L612- cages photosensitize the 1,3-rearrangement of encapsulated cinnamylammonium cation guests from the linear isomer to the higher energy branched isomer when irradiated with UVA light. The rearrangement requires light and guest encapsulation to occur. The Ga4L612- cage-mediated reaction mechanism was investigated by UV/vis absorption, fluorescence, ultrafast transient absorption, and electrochemical experiments. The results support a photoinduced electron transfer mechanism for the 1,3-rearrangement, in which the Ga4L612- cage absorbs photons and transfers an electron to the encapsulated cinnamylammonium ion, which undergoes C-N bond cleavage, followed by back electron transfer to the cage and recombination of the guest fragments to form the higher energy isomer.

  DOI：

  10.1021/jacs.5b06317

文献信息

• KOCHARYAN, S. T.;GRIGORYAN, V. V.;BABAYAN, A. T., ARM. XIM. ZH., 1983, 36, N 8, 523-527
  作者：KOCHARYAN, S. T.、GRIGORYAN, V. V.、BABAYAN, A. T.

  DOI：——

  日期：——
• Base catalysed rearrangements involving ylide intermediates. Part 4. [1,3] Sigmatropic rearrangements of 4-dimethylaminobutenes and [3,3] sigmatropic rearrangements of 3-dimethylaminohexa-1,5-dienes
  作者：Robert W. Jemison、W. David Ollis、Ian O. Sutherland、James Tannock

  DOI：10.1039/p19800001462

  日期：——

  3] sigmatropic rearrangement (11)→(12) of the 9-dimethylamino-9-(1-phenylallyl)fluorene is a stereoselective process (84 : 16) at 170°. Analogous [1,3] rearrangements (16)→(17) of other fluorene derivatives show that the reaction rate is increased by electron donating 9-substituents in the order O– > NMe2 > OMe. Similar substituent effects are observed for the [3,3] Cope rearrangement (25)→(26) of hexa-1

  9-二甲基氨基-9-（1-苯基烯丙基）芴的[1,3]σ重排（11）→（12）是170°的立体选择过程（84:16）。其他芴衍生物的类似[1,3]重排（16）→（17）显示，通过给电子9-取代基的顺序为O – > NMe 2 > OMe ，反应速率得到了提高。对于六-1，5-二烯的[3，3]上交重排（25）→（26），观察到类似的取代基作用。4-苯基，4,4-二甲基和3-二甲基氨基取代基在加速重排（25）→（26）的速率方面特别有效。
• Supramolecular Ga₄L₆^12– Cage Photosensitizes 1,3-Rearrangement of Encapsulated Guest via Photoinduced Electron Transfer
  作者：Derek M. Dalton、Scott R. Ellis、Eva M. Nichols、Richard A. Mathies、F. Dean Toste、Robert G. Bergman、Kenneth N. Raymond

  DOI：10.1021/jacs.5b06317

  日期：2015.8.19

  The K12Ga4L6 supramolecular cage is photoactive and enables an unprecedented photoreaction not observed in bulk solution. Ga4L612- cages photosensitize the 1,3-rearrangement of encapsulated cinnamylammonium cation guests from the linear isomer to the higher energy branched isomer when irradiated with UVA light. The rearrangement requires light and guest encapsulation to occur. The Ga4L612- cage-mediated reaction mechanism was investigated by UV/vis absorption, fluorescence, ultrafast transient absorption, and electrochemical experiments. The results support a photoinduced electron transfer mechanism for the 1,3-rearrangement, in which the Ga4L612- cage absorbs photons and transfers an electron to the encapsulated cinnamylammonium ion, which undergoes C-N bond cleavage, followed by back electron transfer to the cage and recombination of the guest fragments to form the higher energy isomer.